


The Swimming Hole

by CLeighWrites



Category: Supernatural
Genre: Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Consensual Underage Sex, Dom/sub Undertones, First Time Blow Jobs, Frottage, M/M, Sam is 16, Semi-Public Sex, Skinny Dipping, Top Sam Winchester, first time anal fingering, first time frottage
Language: English
Status: Completed
Published: 2019-01-10
Updated: 2019-01-10
Packaged: 2019-10-07 21:38:03
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,840
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17373740
Author URL: https://archiveofourown.org/users/CLeighWrites/pseuds/CLeighWrites
Summary: Sam has come up with a plan to get Dean to realize that he’s grown up, little does he know that Dean has already noticed. What happens when both boys find out that the other had a plan at the swimming hole?





	The Swimming Hole

**Author's Note:**

> Beta’d by my lovely wifey @holyfuckloueh (Tumblr)

Sam wasn’t sure what had changed. He couldn’t be sure if it was because his muscles were finally growing to catch up with the rest of him, or if it was because his voice was finally done cracking every time he spoke. Whatever the reason, Sam wasn’t complaining.

He had spent all summer trying to get some color on his skin and tone up his arms and legs so he wouldn’t look so gangly. He wanted to look more like Dean. Granted, Dean freckled more than he tanned, but at least he didn’t look like a vampire; a wiry, teenage, vampire. Sam had done everything that he could to look more grown up. Doing everything he could so that Dean wouldn’t just see him as his baby brother that needed protecting all the time.

Turning sixteen at the beginning of the summer must have helped. Suddenly he was becoming toned, he had shot up what had to have been 6 inches in a matter of months, and he had decided to let his hair grow out; no more easy to trim bowl cuts for him. He was old enough to be making his own decisions. One of his decisions was to see how much more he could be with his big brother.

Dean had been the one to teach him how to jerk off properly, had shown him what the big deal was with the circle jerks he’d heard so much about, and even taught him how to kiss. That kiss was something Sam would never forget, having Dean’s lips pressed so soft against his, leading him, his tongue so gentle as it reached into his mouth to taste him, teach him how he’s supposed to be with someone else. The thing was, Sam never wanted there to be someone else.

After the kiss, Dean was a little different with Sam. He wasn’t mean exactly, but more distant, and definitely not interested in anymore sex ed lessons. Sam had seen the types of guys Dean looked at, when he didn’t think Sam was paying attention. So Sam decided to be more like what Dean liked, as far as guys went anyways, there was only so far Sam would go to catch his brother’s eye; lace panties and lip balm wasn’t on the list.

They were at Bobby’s this summer which meant there was the swimming hole they were pretty sure only they knew about. They’d been going since they were kids and never saw another soul down there; Sam had a plan. He was going to help Dean work on one of the cars out in the yard, then race Dean down to their swimming spot, then they would go skinny dipping. That’s as far as he’d gotten with the plan, Sam figured he couldn’t be the one doing all the work.

Sam matched Dean in jeans and a t-shirt for working on the car, he didn’t know about Dean, but he had decided to go commando; it would make things easier later. Sam helped lift heavy parts and lifted things for Dean to get under as needed, making a show of how his biceps popped when he’d flex. He kept having to shake his hair out of his face when his hands were busy, but he didn’t mind, after a while the sweat helped keep it in place. Once they got the car running Sam grinned over at Dean and raised his eyebrows.

Dean looked at him suspiciously, “What? Do I have grease on my face?” He bent down to check himself in the mirror.

“No, but it sure is hot,” Sam paused and waited for Dean to look back at him, “Nice day for a swim…”

Dean’s face lit up, “Race ya!”

They both took off like a shot, Dean had him at first, since he was on the right side of the car to start off with, but Sam’s legs were longer than his now. He caught up with Dean quicker than either of them thought he would, and Sam had to make sure he didn’t leave him too far behind, or he might be too pissed for the rest of his plan to work. Sam took the long way around some brush which gave Dean the chance to get ahead of him and beat him to the worn out dock.

“Ha! Can’t beat me little brother!”

“One day, I’m almost bigger than you now,” Sam teased him.

Dean looked him over as they caught their breath, “Yeah, well, you ain’t yet.”

“Ok, last one in’s a rotten egg!” Sam grabbed the bottom of his shirt and pulled it off over his head with one hand, then toed his shoes off. When he looked up Dean was trying not to stare at him. “What is it Dean? Something on me?” He rubbed his hand over his chest and smiled as he spun around, his jeans barely hanging on to his hips now that he’d started to tone up his baby fat.

Dean just shook his head, “Naw man, just...you’ve been working out,” he cleared his throat, “looking good Sammy.”

Sam’s grin widened at his praise and he took in a deep breath as he unbuttoned his pants and lowered the zipper. Dean was still watching him, fully clothed, “Dean are you, uh, you going to swim in your clothes?” He tried for a chuckle, it ended up coming out more on the breathy side of laughing, but he just shrugged it off as he finally shed his pants and socks.

“Umm, yeah. I mean, no. Damn Sammy, what’d you do to my baby brother?”

Sam walked up and stood directly in front of him, they were eye to eye with Dean still in his shoes, “Baby brother’s all grown up now Dean,” Sam leaned in just a tiny bit more and Dean’s breath hitched, “You comin’ or what?” He grinned and ran down the dock, jumping head first into the cool water.

By the time Sam came up for air Dean was half falling down the dock trying to shake his second leg out of his pants. He finally gave up and just sat down to unhook his pants from his shoe and threw them both to the edge of the dock. Sam blushed when he noticed that Dean had also decided against underwear that morning. Despite the coolness of the water, Sam felt himself stiffen at the thought that maybe, just maybe, Dean had the same plan for today.

“Laundry day?” Sam teased as Dean jumped in, landing quite close to where Sam was treading water.

Dean popped up right beside him, shaking the water out of his face before shoving Sam under. When he came back up Sam shook his hair out of his face and gave Dean a look.

“I could ask you the same question there, Sammy,” god damn if Dean wasn’t looking at him through his long as fuck, wet lashes.

Sam’s brain went a little fuzzy, “Yeah, well…” he really couldn’t think of anything to say so he just grinned before splashing Dean with an arm full of water and back swimming to put some distance between them.

“Oh, you little-”

“Not so little anymore big brother,” Sam interrupted him, laughing as he hit him with another wave of water.

Dean ducked under water and Sam couldn’t tell which way he went. He swam away from where he had been, suspecting that Dean would be coming for him. After what seemed like longer than Dean would be able to hold his breath for, Sam started to worry. “Dean!” His pulse quickened and he began looking for air bubbles, swinging his head in every direction to look for clues. “Dean! This isn’t funny!”

A deep throated laugh caught Sam by surprise, and he spun around to find Dean sitting on a clear spot on the bank a little ways away. Sam almost stopped mid-stroke on his way to where he was when he saw that Dean was sitting on a blanket. His head spun, and Dean just laid there with his ankles crossed and his arms folded behind his head. Once Sam got to a clear place to ascend the bank, Dean held his hand out for him, and pulled him up.

Looking around, Sam noticed that there wasn’t just a blanket, there was a cooler, which was full of beer, if Sam had to guess, and a bag full of chips and jerky and other snacks. Sam flushed all over and his semi-hard cock twitched when he realized that Dean had a plan too; and that at least part of it, included a picnic. Sam realized he was just standing there gawking when Dean gestured wide with his arms for him to sit. Suddenly self conscious of his nakedness, Sam sat cross-legged on the other side of the blanket than Dean had been laying on and opened the cooler, pulling out two beers, handing one to his brother.

“Were you planning on having someone out here already? I didn’t mess up your plans did I?” No way Dean had planned on coming out here the same day as he did.

“You might say that,” he reached in the bag, pulled out Sam’s favorite chips, and winked at him as he threw the bag at him.

Sam could feel his whole face turn red as he played with the seam of the chip bag. He laughed to himself and shook his drying hair out of his face, “You know, I kind of had this plan…”

“You don’t say,” Dean took a sip of his beer, but didn’t take his eyes off Sam.

Sam watched how his lips curled around the bottle and his throat bobbed as he swallowed. He realized a second too late, when Dean’s eyes traveled down to his lap, that he was harder than he had been before. He tried to shift in his place, offer himself a little cover, but it was useless. He opened the bag of chips and put them in front of his legs, at least partially blocking his growing erection from his brother’s line of sight. Dean licked his lips, raised his eyebrows, and just grinned at him. Sam couldn’t meet his eye, so he focused on opening his own beer and grabbing some chips.

Dean cleared his throat, “So, these plans of yours…” the question was implied, and Sam honestly didn’t have anything actually planned after getting naked and jumping in the pond.

Sam just smiled and tucked his chin to his shoulder, not being able to hide behind anything, naked on the edge of the pond with nothing but a beer and a bag of chips. Dean sat up then, finished off his beer and leaned across the blanket, stretching out unnecessarily to grab another one out of the cooler. Sam took the opportunity to get a good look at Dean’s body; the shape of his ass as it moved down to his thick bowed thighs, the muscle that flexed in his back as he reached across the blanket, the curve of his tricep, the flick of his wrist when he opened the cooler, and how his skillful fingers wrapped around the neck of the beer bottle.

So much for trying to hide his hard on. Sam took a couple chugs of beer, downing about half of it and laid down flat on his back, tossing one of his arms over his head, holding his bottle at his hip. He closed his eyes and watched the patterns that the tree filtered sunlight made on the backs of his eyelids. He felt his muscles relax as he took in a deep breath, it smelled like pond water, sunlight, and...was that whiskey? He peeled open one eye and turned his head toward Dean who had one eyebrow quirked up and his eyes noticeably zeroed in on Sam’s pelvic region.

Dean was holding a bottle of Jack now, he took a long sip, grimaced, and offered the bottle to Sam. Sam rolled over on his side, resting his head on the heel of his hand and reached for the bottle with his other. He tried to focus on the bottle and keeping his eyes north of Dean’s abdomen. He was laying just like Sam, and it was so hard for him not to follow the lines of Dean’s torso, over his hips, down his legs. Sam tried to take just as big of a sip of the whiskey as Dean had, but he wasn’t prepared for the burn and he almost choked on it.

Dean took the bottle back from him and leaned farther over to slap him on the back, “Easy there Tiger. I’ve never given you whiskey before.”

“I’m fine,” Sam gasped as he reached for the arm Dean was using to beat on his back with, “I’m-” Sam’s words were cut off when he realized how close Dean was now, practically leaning over him, his chest in his face, “fine.”

Sam tried to look away, but looked down without thinking and saw that Dean was just as hard as he was. His mouth went dry, from more than just the whiskey, and when Sam lifted his eyes back up to meet Dean’s he stopped breathing. Even with making plans, and trying his damnedest to get Dean to look at him just like this, Sam had never actually hoped that it would happen. Sam licked his lips reflexively when Dean did the same, and he mimicked Dean, closing his eyes, when he leaned down.

Sam felt the same pull in his gut he did the first time, when Dean was teaching him how to kiss, and he got just as lightheaded from it. Dean’s lips were soft and pliant against Sam’s, and his tongue was hot from the whiskey, Sam could feel the burn of it on his lips. Sam dropped his hold on Dean’s arm laying flat on his back, and Dean followed him down. He didn’t settle on top of him, like Sam would have liked, but he did press up alongside of him with each of his hands on either side of Sam’s head. Sam took advantage of not needing his arms for balance and wrapped them around his brother, one hand going to the back of his neck, and the other wrapping under his arm and around his back.

Sam tried to pull Dean on top of him, but he resisted. Sam groaned into Dean’s mouth and tried to twist his hips into him, but he held him firm. Sam tried to kiss Dean hard, but he pulled back, with an equally amused and irritated look on his face.

Sam said, “What the hell, Dean?” At the same time that Dean said, “What are ya trynna do Sammy?”

Dean laughed, but Sam just huffed, “There’s the little brother I know and love,” Dean tried to joke, but Sam wasn’t having it.

“It’s not funny Dean,” Sam tried to roll away instantly embarrassed, but Dean wouldn’t let him.

“Sammy…” Dean sang his name and tried to catch his eye, but Sam squeezed his eyes shut.

Dean put his hand on the side of Sam’s face, rubbing his thumb over Sam’s cheek. When that did nothing he slipped his thumb over Sam’s lips then leaned in to kiss him again. Sam couldn’t help himself, kissing back, but when Dean’s tongue sneaked out again Sam pulled back, breaking the kiss.

It was Dean’s turn to huff and he sat back, one knee pulled up that he propped his arm on to hold his head up with. He looked down at Sam and waited for an explanation. Sam avoided his brother’s gaze and stared up at the trees. He took a deep breath, then turned to face him.

“Why won’t you- do you not want-”

“What? To fuck you Sammy? Are you asking me if I want to fuck my baby brother?”

“No!” Sam stopped, not believing his own lie, “Well, yes. I know it’s not because I’m a guy, I’ve seen the way you look at some guys when you think I’m not looking. I’ve- I’ve seen the way you’ve looked at me.”

“Okay. And now you’re going to tell me that, in addition to the other things you’ve done with me, you want to add your first time to the list? Seriously Sammy?”

“Dean, I-”

“No Sammy, the way we were raised, I get it, you didn’t have close guy friends to goof off with and do stupid shit with,” Sam shirked away at that, scrambling up and tucking his knees up to his chest, “No Sammy, dammit,” Dean reached for him but he jerked away, feeling the tears well up in his eyes. “Man, I’m not saying that what we did was stupid, okay? Fuck, Sammy?” Dean leaned over and got in front of him, but Sam turned away.

He refused to turn and look at his brother, embarrassment and shame freezing him in place as his tears slid silently down his face. He took a deep, shaky breath and laughed without humor, “What do you want from me Dean? Obviously I wasn’t the only one with a plan here today.”

Dean didn’t say anything for a while. Sam had almost given up, but just before he moved to stand, Dean finally spoke, “Look,” Sam stopped, but still didn’t turn to face him, “I don’t know what to tell you. I mean, if I tell you that I’ve been thinking about fucking you for, shit, at least the past year, what does that make me? Do you have any idea how fucked up I felt doing those things to you, with you, whatever?”

Sam did turn to face Dean at that, “Dean, I asked you to. You didn’t-”

“Sammy, as much as I would like to believe that, I can’t. I’m your big brother, I’m supposed to protect you, not- not…”

Sam turned and put his hand on Dean’s arm, Dean let him.

“How fucked up am I Sammy?” He sounded wrecked.

“Dean? Look at me,” Sam moved his hand from his arm to his chin and turned his face to look at him. “You’re not fucked up, at least, no more than I am. We’re the same kind of fucked up. I’ve never felt about anyone else the way I feel about you.”

“That don’t make it right, Sammy. You’re still a kid, I shouldn’t even be looking at you, forget the fact that you’re my brother.”

“But I am your brother. And you’re right, the way we were raised is super fucked up, but that doesn’t change the way I feel about you. And I want this, Dean, I want you. I can’t even tell you how amazing it felt that first time, when you were teaching me how to kiss. Or how embarrassed I was when I came so quick when you jerked me off for the first time.” Sam flushed at his own words and Dean finally looked him in the eye.

Dean grinned and moved Sam’s hand off of his face, but kept it on his arm, keeping contact. Sam was grateful for that, at least he wasn’t pushing him away completely. They sat in silence for a little while, Dean rubbing little patterns on the back of Sam’s hand.

Dean chuckled to himself, “Yeah, you did blow your load pretty quick that first time.”

Sam shoved him playfully, “Yeah, yeah, yeah...well, one day I’ll get you that quick and see how you like it.”

Dean play shoved him back, “Never gonna happen baby brother.”

They started to wrestle each other, careful not to knock each other’s heads into the cooler. Somehow Sam ended up pinning Dean and he just laughed up at him. They both stopped laughing about the same time as they looked at each other. Sam could feel his blood rushing south as he swung his mostly dry hair out of his face and leaned down to kiss his asshole big brother. Sam kept his eyes open this time, gauging Dean’s response; he closed his eyes when Dean did and put everything he was feeling into that kiss. Dean let him take the lead, setting the pace and depth of their second attempt.

Dean didn’t stop him as he let his hands trail down his chest. Dean didn’t stop him as Sam moved one of his legs in between his. Dean didn’t stop him as he slid his hands down his side to his hips. Dean didn’t even stop him as he started kissing his way down his body. Surprisingly, Dean didn’t stop him when he began to work his dick to full hardness, and started placing light, teasing kisses along his thick thighs.

Sam had never done this before, it wasn’t something he’d ever seen Dean do either, so he was just making things up as he went. The moans he was getting out of Dean was all the validation that he was doing the right thing Sam needed. Sam knew from when Dean would jerk him off that he really liked to pay attention to the vein and tip, so he started by licking him from base to tip with his tongue wide and swirled his tongue around his crown when he got to the top. Dean’s hips bucked and Sam willingly took Dean’s head into his mouth. He kept his tongue flat on the underside when he took Dean back into his mouth. He pulled his tongue back in and hallowed his cheeks, figuring they called it sucking dick for a reason.

Dean hissed through his teeth and called out a breathy, “Sammy,” and damn if that didn’t make Sam’s dick jump.

Sam repeated the same action a few more times before adding his hand to the base since he couldn’t fit all of Dean’s dick into his mouth. He rubbed his thumb along the tender vein as he kept bobbing and sucking at his brother’s hard cock. Not too long after he tasted a tangy taste and when he pulled away he saw precome gathered on his tip, he used his thumb to smear it around. Dean moaned again and Sam went to swallowing him down again, but Dean’s hand on his cheek stopped him.

Sam looked at him wide-eyed, panicked that maybe he had done something wrong before Dean stopped him from overthinking, “Come’re.”

Dean kept his hand on Sam’s face as he pulled him up to be face to face with him. He kissed him deeply, smashing his lips into his; it was all teeth and tongue. Sam reflexively rocked his hips, seeking friction and ended up thrusting against Dean’s cock. They both groaned into each other’s mouths, then Dean laughed a little. Sam thrust his hips again, and Dean put his hand on his shoulder. Sam pulled back and went to pull himself off of his brother, but Dean kept pressure on his shoulder, holding him in place.

“What, what is it? Did I-”

“No, no, Sammy, you’re fucking perfect. I just,” he squirmed underneath of him, “I wanna show you something.”

“Like, now?” Sam’s blood was not in his brain, and he was slow to follow Dean’s meaning.

“Yes, like now.” Dean reached between them and grabbed himself, stroking himself before he looked back up at Sam.

Sam went to pull his knees up and straddle Dean’s hips, thinking that things were speeding up, but Dean just slaps on this lopsided grin and shakes his head, “No Sammy, not that right now.”

“Then wha-”

“Just, let me show you something,” his voice took on that ‘you better listen to me, I’m the big brother’ tone and Sam settled back down onto his knees, no longer knowing what it was he was supposed to be doing.

Dean licked a solid stripe up his palm and the tips of his fingers then arranged Sam’s hips to be level with his before reaching around both of their cocks, squeezing them both together and started rubbing up and down their pressed shafts at a slow but steady pace. Sam almost lost his ability to hold himself up as the sensation of Dean’s dick jerking and pulsing right up against his own sent him dangerously close to another quick release. Sam tried to steady his breathing and focus more on kissing Dean than what he was doing with them between them.

“Damn, Sammy,” Dean breathed against Sam’s lips, “feel so fucking good.”

Sam was only able to muster a breathy, “Mmmmm, Dean,” in reply.

Sam was determined not to come first, but he was so close, he couldn’t hold on any longer.

“It’s okay Sammy,” Dean bit Sam’s bottom lip and tweaked his wrist, “it’s okay.”

“No, Dean, don’t wanna,” he groaned as Dean quickened his pace and kissed him again.

Sam’s arms started to shake and he could barely breathe let alone hold himself up much longer. He got an idea and wrapped his arm around Dean’s shoulders then pulled him up as he leaned back on his knees, balancing his weight as well as Dean’s. Dean locked his ankles behind Sam’s back and never let up on his ministrations. With this new angle Sam could hold on a little longer, and he got an idea. He had more access now, and he had seen it done, although he had never done, nor had it done, himself. He brought one hand up to his mouth and sucked his two middle fingers into his mouth, getting them as wet as possible.

“What are you- oh!” Dean was cut off by Sam teasing his hole with his spit-slick finger.

Dean buried his head in the crook of Sam’s neck, breathing heavily as Sam toyed with him, testing out his reactions. He tensed and almost stopped his strokes when Sam slipped inside him with his first phalange. Dean squeezed their cocks harder together as Sam worked his finger in farther. He whispered words of encouragement to Sam as he kissed and sucked at his neck and ears, and Sam kept working his way in.

“Add the other,” Dean’s breath was hot in his ear and Sam pulled out his already inserted finger to the nail and added in the other.

When he was about in to his first knuckle he crooked his fingers to get them in farther but Dean damn near jumped out of his lap, all but screaming his name. An unexplainable sense of pride and something else bloomed in his chest that he could take his brother to pieces in such a way. He did it again and felt what must be his prostate at his fingertips. Sam massaged the bundle of nerves until Dean was an absolute sweaty mess in his lap, hardly able to form words.

“Come for me, Dean.” Sam’s voice was, thankfully deep, and commanding when he spoke and with the next push of Sam’s fingers and stroke of Dean’s hand he was spilling white hot all over both of them.

Sam removed his fingers, and was unable to control himself any longer. Feeling his brother’s orgasm pulsing out of him, he came soon after, Dean stroking them both through their aftershocks. Once they were both done, Sam leaned back, rolling slightly and taking his big brother with him. Dean lay tucked into Sam’s side stroking patterns on his, regrettably hairless, chest, while Sam tried to wrap his head around everything that had just happened. Not just that they had finally done something together like that, but how Sam had reacted to the situation; he liked to be the one in control. He didn’t really know what it meant, but he knew that’s what he liked. Somewhere in the back of his mind he filed that away, along with how Dean seemed to enjoy being manhandled, for lack of a better word.

They lay tangled together, with come drying on their stomachs, until the sun started to set and it would almost be too cold to swim back to the dock. Dean yawned when Sam tapped him to get up.

“Yeah, yeah,” he stood up and stretched, “damn Sammy...if I had known that you’d-”

“I haven’t. Before. I’ve never…” he stood up, mimicking Dean in a full bodied stretch.

“Really?” Dean looked genuinely surprised. “Hmm. Well, in that case…” he wiggled his eyebrows at him, “I can’t wait to see what else you come up with, little brother.”

Sam felt his whole body flush at the praise and he started to reach for the cooler but Dean stopped him with a hand on his shoulder, “Leave it, I feel like another swim tomorrow.”

“Really Dean,” Sam faked annoyance, but he was already starting to stiffen at the thought of another picnic with his big brother.

“Oh, yeah,” Dean winked at him then jumped back into the pond and started making his way toward the dock.

Sure, Sam wasn’t sure what exactly had changed that summer, but he definitely wasn’t complaining.

**Author's Note:**

> Thanks for reading! Don't be shy, let me know what you think!


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